The present invention provides hexynyl alkanoates having the structure: ##STR2## wherein R represents hydrogen or ethyl and uses thereof for their organoleptic properties in augmenting or enhancing the aroma and/or taste of consumable materials.
Materials which provide sweaty, animalic, leathery, floral, anisic, green, petitgrain, neroli and magnolia aromas with fruity, green herbaceous, floral, chamomile, orange flower and neroli topnotes are highly desirable in the art of perfumery. Many of the natural materials which provide such fragrances and contribute such desired nuances to perfumery compositions are high in cost, vary in quality from one batch to another and/or are generally subject to the usual variations of natural products.
By the same token, materials which can provide green, "Marquisa", passion fruit, sweet, fruity, brown sugar-like, and maltol-like aromas with green, "Marquisa", passion fruit-like fruity, brown sugar-like, maltol-like, maple and creamy taste profiles are highly desirable in the art of flavoring foodstuffs, chewing gums, toothpastes, medicinal products and chewing tobaccos. Many of the natural materials which provide such flavor notes and contribute such desired nuances to flavorant compositions are high in cost, vary in quality from one batch to another and/or are generally subject to the usual variations of natural products.
There is, accordingly, a continuing effort to find synthetic materials which will replace, enhance or augment the essential flavor and fragrance notes provided by natural essential oils or compositions thereof. Unfortunately, many of these synthetic materials either have the desired nuances only to a relatively small degree or else contribute undesirable or unwanted odor to the compositions. The search for materials which can provide a more refined passion-fruit flavor, for example, has been difficult and relatively costly in the areas of both natural products and synthetic products.
Artificial flavoring agents for foodstuffs have received increasing attention in recent years. For many years such food flavoring agents have been preferred over natural flavoring agents at least in part due to their diminished cost and their reproducible flavor qualities. For example, natural food flavoring agents such as extracts, concentrates and the like are often subject to wide variations due to changes in quality and type and treatment of raw materials. Such variations can be reflected in the end products and result in unfavorable flavor characteristics in said end products. Additionally, the presence of the natural product in the ultimate food may be undesirable because of increased tendency to spoil. This is particularly troublesome in food and food uses where such products as dips, soups, chips, sausages, gravies, dairy desserts and the like are apt to be stored prior to use.
The fundamental problem in creating artificial flavoring agents is that the artificial flavor to be achieved be as natural as possible. This generally proves to be a difficult task since the mechanism for flavor development in many foods, medicinal products, chewing gums and toothpastes is not completely known. This is particularly noticeable in products having passion fruit-like flavor characteristics.
Even more desirable are products which can serve as substitutes for difficult-to-obtain and natural perfumery oils and, at the same time, substitute for natural flavoring ingredients in foodstuffs, chewing gums, medicinal products, toothpastes and chewing tobaccos.
Bicchi, et al, Chem.Abstracts, Volume 98, Abstract No. 52004x (Title of paper: "Considerations And Remarks About Honey Volatile Components", "Recent Dev. Food Anal. Proc. Eur. Conf. Food Chem. 1st, 1961 (Published 1982), pages 137-42) discloses the presence in honey volatiles of 3-hexynyl acetate as well as cis-3-hexenyl butyrate having the structures, respectively: ##STR3##
The 3-hexynyl acetate has a fruity, green aroma profile with balsamic and cinnamic topnotes. In addition, the 3-hexynyl acetate has a sweet and green aroma and taste profile at 1 ppm.
Arctander "Perfume And Flavor Chemicals (Aroma Chemicals)" published in 1969 discloses ethyl-2-heptynoate having the structure: ##STR4## at Monograph 1261. It is described by Arctander as having a "powerful, leafy-green odor of moderate to poor tenacity". Arctander at Volume II, Monograph 2425 discloses octyl octynoate having the structure: ##STR5## as having an "oily-green, mildly leafy and somewhat fatty odor of considerable tenacity". ##STR6## is a known compound (Environmental Protection Agency Cumulative Supplement II, Substantive Name Index CAS. No. 1002-28-4).
However, nothing in the prior art discloses the unexpected, unobvious and advantageous organoleptic properties of the compounds of our invention defined according to the structure: ##STR7## wherein R represents hydrogen or ethyl.